The transformation of steroids by microorganisms has been widely studied and documented. Apparently, the earliest such work was by Mamoli and Vercellone in 1937, Ber. 70, 470 and Ber. 70, 2079. They disclosed the reduction of 17-ketosteroids to 17.beta.-hydroxysteroids by fermenting yeast. More recently, Peterson and Murray disclosed the 11.alpha.-hydroxylation of progesterone with the fungus Rhizopus nigricans; see, U.S. Pat. No. 2,602,769 (1952). Also recently, Kraychy et al. in U.S. Pat. No. 3,684,657 (1972) discloses the selective microbiological degradation of steroidal 17-alkyls by fermenting a steroid containing at least 8 carbons in the 17-alkyl side chain with Mycobacterium sp. NRRL B-3683 to prepare androst-4-ene-3,17-dione, androst-1,4-diene-3,17-dione, and 20.alpha.-hydroxymethyl-pregna-1,4-dien-3-one. Even more recently, Marsheck et al. in U.S. Pat. No. 3,759,791 (1973) disclose the selective microbiological preparation of androst-4-ene-3,17-dione by fermenting a steroid of the cholestane or stigmastane series containing at least 8 carbons in the 17-alkyl side chain with Mycobacterium sp. NRRL B-3805.
Compound III of the subject invention has been disclosed by Wang and Sih in 1963 (Biochem. 2: 1238-1243) as an intermediate in the degradation of androst-4-ene-17.beta.ol-3-one by Nocardia restrictus. The open ring form of compound 1, 7.alpha.-methyl-perhydroindanedione-(1,5)-[.beta.-propyl alcohol-(4)], has been disclosed by Schubert et al. in 1964 (Steroids 4: 581-586) as an intermediate in the degradation of progesterone by Mycobacterium smegmatis.